Freidal crafts reaction

Chemistry Level 3

How many of these do not undergo Freidal crafts alkylation reaction

Nitro benzene
Amino benzene
methyl benzene
Benzene
Benzoic acid
Benzene sulphonic acid
$\ce {C6H5COO^-}$

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This is a part of my set Aniket's Chemistry Challenges . (BEST OF JEE - ADVANCED)

1 3 4 6 5 7 2

1 solution

Aniket Sanghi
Mar 21, 2016

1,2,5,6 are correct answers

Why not 7th one

Mayank Hooda - 5 years, 2 months ago

It is stable in itself due to equivalent resonance structures

Aniket Sanghi - 5 years, 2 months ago

Then assuming you are right that there is no resonance in 7th one....explain how benzoic acid is weaker than formic acid?( as you infer no cross conjugation)

Mayank Hooda - 5 years, 2 months ago

@Mayank Hooda – I can assure you that the answer is correct as the question is original......I will try to explain :P

Aniket Sanghi - 5 years, 2 months ago

@Aniket Sanghi – Can you give me the source please?

Mayank Hooda - 5 years, 2 months ago

@Mayank Hooda – And even if no resonance takes place in 7th part...there is still a strong -I effect of COO- (which is obviously more than that of Cl) so it has to be a deactivating group in any case...

Mayank Hooda - 5 years, 2 months ago

@Mayank Hooda – First of all COO- shows +I effect as there is electron rich region between it's bonds due to equivalent resonance which it inserts into benzene ring.

Sarvesh Yadav - 4 years, 1 month ago

I agree with Mayank Hooda . Even if the carboxylate part is stabilized due to equivalent resonating structures, the key atom of the benzene ring is connected to two electronegative atoms (the O's) implying that it will exert a strong -I effect thereby deactivating the ring towards Friedel Crafts Reaction.

Prakkash Manohar - 5 years, 1 month ago

@Prakkash Manohar – Have you seen anywhere or its your own theory........my ans is verified by fiitjee

Aniket Sanghi - 5 years, 1 month ago

@Aniket Sanghi – (verified by fiitjee)...I myself am enrolled in fiitjee. If you asked your teacher (or your teacher told you), its great and if you saw this in the package or any other fiitjee material, please state it so that I can check it out. Thanks!

Prakkash Manohar - 5 years, 1 month ago

@Prakkash Manohar – You can check it in the package of EAS

Aniket Sanghi - 5 years, 1 month ago

Why does nitrobenzene not undergo friedel crafts reaction? It yields meta product.

Milind Blaze - 5 years, 2 months ago

No it don't undergo freidal crafts reaction as nitro is highly deactivating group

Aniket Sanghi - 5 years, 2 months ago

Freidal crafts reaction

This is a part of my set Aniket's Chemistry Challenges . (BEST OF JEE - ADVANCED)

1 solution

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